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Methanesulfonic Acid → 2(4-Isoxazol-4-yl-phenoxy)-ethylamine

HRID 413311
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HRID 413311 반응식
C(OC(=O)[NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[N:22][O:23][CH:24]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1.CS(O)(=O)=O.[OH-].[Na+]>C(Cl)Cl.O>[O:23]1[CH:24]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][CH2:11][NH2:10])=[CH:15][CH:16]=2)[CH:21]=[N:22]1
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참가 물질

6

반응물 3

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 20587952HCID 20587952, 화합물

생성물 1

HCID 185329642(4-Isoxazol-4-yl-phenoxy)-ethylamine수율 53%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

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온도
35 °C

실험 절차

[2-(4-Isoxazol-4-yl-phenoxy)-ethyl]-carbamic acid benzyl ester (1.00 g, 2.81 mmol) was dissolved in methylene chloride (14 ml) and methanesulfonic acid (2.73 ml, 42.2 mmol) was added. The resulting mixture was heated to about 35° C. for about two hours, and was then diluted with methylene chloride and water. The pH of the mixture was adjusted to about 12 with 5N sodium hydroxide, and the mixture was extracted with methylene chloride. The combined extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by column chromatography (20% methanol/methylene chloride) to afford 202 mg (53% yield) of the desired amine. LRMS ([M+H]+)=205.3.

후처리

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude product was purified by column chromatography (20% methanol/methylene chloride)

출처 및 근거

ORD 기록
ord-0083f4c3355f405f89f06b0a90b79be4
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06566377B2

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